Category: alcohols-buliding-blocks

Kuzniewski, Christian N. published the artcileSynthesis, Profiling, and Bioactive Conformation of trans-Cyclopropyl Epothilones, Application In Synthesis of 57044-25-4, the publication is Helvetica Chimica Acta (2019), 102(5), n/a, database is CAplus.

A series of new 3-deoxy-C(12),C(13)-trans-cyclopropyl-epothilones have been prepared, bearing benzothiazole, quinoline, thiazol-5-ylvinyl, or isoxazol-3-ylvinyl side chains (I – IV, resp.). For analogs with fused aromatic side chains, macrocyclic ring-closure was based on ring-closing olefin metathesis (RCM) of a precursor incorporating the fully elaborated heavy atom framework of the target structure (including the side chain moiety), while side chain attachment for the thiazole and isoxazole-containing 16-desmethyl analogs was performed only after establishment of the macrolactone core. Two approaches were elaborated for a macrocyclic aldehyde as the common precursor for the latter analogs that involved ring-closure either by RCM or by macrolactonization. Benzothiazole- and quinoline-based analogs were found to be highly potent antiproliferative agents; the two analogs with a thiazol-5-ylvinyl or an isoxazol-3-ylvinyl side chain likewise showed good antiproliferative activity but were significantly less potent than the parent epothilone A. Surprisingly, the desaturation of the C(10)-C(11) bond in these analogs was associated with a virtually complete loss in antiproliferative activity, which likely reflects a requirement for a ca. 60 ° C(10)-C(11) torsion angle in the tubulin-bound conformation of 12,13-trans-epothilones.

Helvetica Chimica Acta published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application In Synthesis of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Salaun, J. published the artcileSmall rings. XXX. Ring expansion of cyclopropanols. 1-(Halomethyl)-, 1-(hydroxymethyl)-, 1-vinyl-, 1-acylcyclopropanols, and oxaspiropentanes to cyclobutanones, Safety of (1-Bromocyclopropyl)methanol, the publication is Tetrahedron (1974), 30(11), 1413-21, database is CAplus.

1-(Hydroxymethyl)-, 1-(tolysulfonyloxymethyl)-, 1-(bromomethyl)cyclopropanol, and oxaspiropentane (I), prepared from methylenecyclopropane, underwent ring expansion to form cyclobutanones. 1-Vinyl-, 1-(1-cyclopentenyl)- and 1-(1-cyclohexenyl)cyclopropanol, prepared from (ClCH2)2CO underwent similar ring expansion. 1-Cyclopropylcyclopropanol under similar conditions gave cyclopropyl Et ketone. II with NaOMe followed by treatment with ClSiMe3, gave cyclobutanone III.

Tetrahedron published new progress about 50915-29-2. 50915-29-2 belongs to alcohols-buliding-blocks, auxiliary class Cyclopropanes, name is (1-Bromocyclopropyl)methanol, and the molecular formula is C4H7BrO, Safety of (1-Bromocyclopropyl)methanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bruusgaard-Mouritsen, Maria A. published the artcileFacial contact dermatitis caused by cosmetic-relevant allergens, Synthetic Route of 70445-33-9, the publication is Contact Dermatitis (2021), 85(6), 650-659, database is CAplus and MEDLINE.

Facial allergic contact dermatitis caused by cosmetic products is common. New allergens in cosmetics continuously emerge. To investigate characteristics of patients with facial dermatitis (FD) between 2010 and 2019 including patch test results from cosmetic-related allergens and a new test series with cosmetic-relevant natural ingredients (CRNIs). This is a retrospective study analyzing demographics, clin. characteristics according to MOAHLFA index (male; occupation; atopic dermatitis; hand; leg; face; age ≥ 40 years), and patch test results to 27 cosmetic-relevant allergens in FD patients. A prospective study evaluating a screening test series with CRNIs in consecutive FD patients for 1 yr was also conducted. These patients received a questionnaire for collecting extra characteristics (eg, concerning quality of life). Of 8740 tested patients, 2292 (26.2%) had FD. Of these, 30.6% had cosmetic-induced FD. The most common cosmetic-related allergens were fragrances and preservatives. The most common patch test-pos. CRNIs were hydroperoxides of limonene and linalool, and propolis. Potato and peanut were rare, but the most common prick test-pos. CRNIs, however, without any relation to the use of cosmetic products. FD affected nearly all patients′ quality of life and caused limitations to their daily life. Updated management and quick diagnosis of FD is important to avoid neg. impact on patients′ quality of life.

Contact Dermatitis published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C11H24O3, Synthetic Route of 70445-33-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Rubert, Josep published the artcileA Screening of Native (Poly)phenols and Gut-Related Metabolites on 3D HCT116 Spheroids Reveals Gut Health Benefits of a Flavan-3-ol Metabolite, Product Details of C8H8O3, the publication is Molecular Nutrition & Food Research, database is CAplus and MEDLINE.

Epidemiol. evidence suggests that a reduced risk of colorectal cancer (CRC) is correlated with high consumption of fruits and vegetables, which are major sources of fiber and phytochems., such as flavan-3-ols. However, it remains unknown how these phytochems. and their specific gut-related metabolites may alter cancer cell behavior. A focused screening using native (poly)phenols and gut microbial metabolites (GMMs) on 3D HCT116 spheroids is carried out using a high-throughput imaging approach. Dose-responses, IC50, and long-term exposure are calculated for the most promising native (poly)phenols and GMMs. As a result, this research shows that (poly)phenol catabolites may play a key role in preventing cancer propagation. Indeed, μM concentration levels of (4R)-5-(3′,4-dihydroxyphenyl)-γ-valerolactone significantly decrease spheroid size at early stages of spheroid aggregation and gene expression of matrix metalloproteinases. A chronic exposure to (4R)-5-(3,-d4ihydroxyphenyl)-γ-valerolactone may lead to a reduced CRC risk. Daily intake of monomeric, oligomeric, and polymeric flavan-3-ols may increase the colonic concentrations of this metabolite, and, in turn, this compound may act locally interacting with intestinal epithelial cells, precancerous and cancer cells.

Molecular Nutrition & Food Research published new progress about 621-37-4. 621-37-4 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Phenol,Natural product, name is 3-Hydroxyphenylacetic acid, and the molecular formula is C8H8O3, Product Details of C8H8O3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Price, David A. published the artcileHigh throughput synthesis of functionalized 1,3-diones and subsequent heterocycle formation, Recommanded Product: 3,3,3-Trifluoropropan-1-ol, the publication is Synlett (2002), 1170-1172, database is CAplus.

Treatment of 3,5-heptanedione with iodosylbenzene followed by reaction with aliphatic and benzylic alcs. ROH [R = F₃CCH₂CH₂, EtCMe₂, 3-MeOC₆H₄CH₂, PhO(CH₂)₃, cyclopropylmethyl, etc.] gave the corresponding 4-alkoxy-3,5-heptanediones, which in situ underwent heterocyclization with hydrazine to afford alkoxy-substituted pyrazoles I in 10-40% total yields.

Synlett published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Recommanded Product: 3,3,3-Trifluoropropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bogdanov, A. V. published the artcileSynthesis of New (2-Acetamido)phenylglyoxylamides Containing an Acetal Fragment, Application of 4,4-Diethoxybutan-1-amine, the publication is Russian Journal of Organic Chemistry (2019), 55(1), 121-123, database is CAplus.

Mild opening of the five-membered ring in 1-acetylisatins by the action of an equimolar amount of 4,4-diethoxybutan-1-amine afforded 2-(2-acetamidophenyl)-N-(4,4-diethoxybutyl)-2-oxoacetamides in almost quant. yield.

Russian Journal of Organic Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Application of 4,4-Diethoxybutan-1-amine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Smolobochkin, A. V. published the artcileTandem intramolecular cyclisation/1,3-aryl shift in N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of 3-benzylidene-1-pyrrolines, Application of 4,4-Diethoxybutan-1-amine, the publication is RSC Advances (2017), 7(80), 50955-50960, database is CAplus.

In this article, a novel tandem reaction, which transformed N-(4,4-diethoxybutyl)imines into 3-arylidene-1-pyrrolines, was described. The substrate scope of the starting acetals included arenes with electron-donating and withdrawing groups. The X-ray study of products confirmed the E-stereochem. of the double bonds formed. The best yields (99%) were found in boiling xylene in the presence of TsOH (or 2-nitroresocinol) during 40 (50) hours. The study of substituents effect on the course of the reaction revealed that cascade process took place, combining acid-catalyzed intramol. cyclization of N-(4,4-diethoxybutyl)imines and unusual 1,3-sigmatropic shift of the aryl fragment. Cyclic imines that were formed in high/excellent yields were of interest both from the viewpoint of their biol. activity and synthetic usefulness.

RSC Advances published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C6H12N2O, Application of 4,4-Diethoxybutan-1-amine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Smolobochkin, A. V. published the artcileCyclization of 1-(4,4-diethoxybutyl)-3-aryl(thio)ureas to 2-arylpyrrolidines and 2,3′-bipyrrole derivatives, Quality Control of 6346-09-4, the publication is Russian Chemical Bulletin (2016), 65(3), 731-734, database is CAplus.

A reaction of 1-(4,4-diethoxybutyl)-3-phenylthiourea with resorcinol, 2-methylresorcinol, pyrogallol and hydroquinone in chloroform in the presence of trifluoroacetic acid leading to 2-aryl-1-(N-phenylcarbamothioyl)pyrrolidines I [R = H, Me, OH] and II has been described. The compounds such as 1-(4,4-diethoxybutyl)-3-aryl(thio)ureas R¹NHC(X)NH(CH₂)₃CH(OC₂H₅)₂ [R¹ = C₆H₅, 4-H₃COC₆H₄, 4-BrC₆H₄; X = O, S] in the presence of an acid catalyst undergo intramol. cyclization and dimerization with the formation of 1,1′-bis(N-arylcarbamo(thio)yl)-2,3′-bipyrrole derivatives III.

Russian Chemical Bulletin published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C18H26ClN3O, Quality Control of 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Smolobochkin, A. V. published the artcileSynthesis of functionalized diarylbutane derivatives by the reaction of 2-methylresorcinol with γ-ureidoacetals, Recommanded Product: 4,4-Diethoxybutan-1-amine, the publication is Russian Journal of General Chemistry (2015), 85(7), 1779-1782, database is CAplus.

The synthesis of the target compounds was achieved by a reaction of N-(4,4-diethoxybutyl)urea derivatives (urea acetals) with 2-methyl-1,3-benzenediol (methylresorcinol, phenol derivative). The title compounds thus formed included N-[4-bis(2,4-dihydroxy-3-methylphenyl)butyl]urea derivatives A reaction of N-(4,4-diethoxybutyl)-N’,N’-dimethylurea with 2-naphthalenol (phenol analog) gave N,N-dimethyl-N’-[3-(14H-dibenzo[a,j]xanthen-14-yl)propyl]urea.

Russian Journal of General Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C17H14F3N3O2S, Recommanded Product: 4,4-Diethoxybutan-1-amine.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Smolobochkin, A. V. published the artcileInteraction of 1,1′-(hexane-1,6-diyl)bis[3-(4,4-diethoxybutyl)urea] with resorcinol derivatives. Synthesis of bisarylpyrrolidines, Quality Control of 6346-09-4, the publication is Russian Journal of General Chemistry (2015), 85(2), 517-519, database is CAplus.

In this letter to the editor, the synthesis of 2-aryl-pyrrolidines from 1,1′-(hexane-1,6-diyl)bis[3-(4,4-diethoxybutyl)urea] with resorcinol derivatives is presented. Of note, when chloroform, benzene or acetone solvents were used with trifluoroacetic acid catalyst, complex mixtures of polymers were formed. However, using water in diluted sulfuric acid presented the desired products.

Russian Journal of General Chemistry published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C4H3Cl2N3, Quality Control of 6346-09-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts